Oakland Vacations from $194
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Quality Inn Pittsburgh Airport
Save 100% on your flight
Price was $291, price is now $194 per person
$194
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.4/10 Good! (828 reviews)
I liked that it was safe. I felt comfortable with it being my daughter and I. Catching a taxi was a bit difficult but it came eventually took us to Robinson Mall. Getting back was another story, thank God for good Samaritans who dropped us back
Reviewed on Aug 23, 2025
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Save 100% on your flight
Price was $434, price is now $239 per person
$239
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Changed rooms 3 times as TV wasn’t working. Coffee machine not working.
Easy to walk to restaurants. Quiet.
Reviewed on Aug 24, 2025
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Save 100% on your flight
Price was $634, price is now $375 per person
$375
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.2/10 Very Good! (2,992 reviews)
The parking situation is ridiculous. $44/night to valet park a car added to the price of an underwhelming, outdated room bodes very poorly for the performance of the hotel, especially with the NFL draft coming across the street in less than a year. Room smelled musty and was considerable warmer than the 68 degrees the in room thermostat indicated. And the 32 inch box tv without any streaming capabilities really adds to the outdated feeling of the room. An underwhelming experience for $250 when room and parking are added together.
Reviewed on Aug 24, 2025
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $817, price is now $495 per person
$495
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
The property was great the and the sfaff were awesome.
Reviewed on Aug 17, 2025
Renaissance Pittsburgh Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $1,112, price is now $711 per person
$711
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9/10 Wonderful! (1,006 reviews)
Hotel had everything we needed; Bed was super comfy. We were in town for Baseball and Football. Both stadiums are within short walking distance. Conveniently located only a block away from the express bus that you can take to and from the airport.
only negative was that the bathroom could use an update, tub was slow to drain, taps on the sink and tub needed adjusting and the wallpaper was peeling off the wall. That being said would 100% stay again!!
Reviewed on Aug 25, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Aug 27 to Aug 28
$148 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (414 reviews)
"Courtyard by Marriott is always a good and reliable choice. This hotel seemed a step above the usual. Lobby welcoming, dining area, friendly staff, rooms. Super location. Not cheap. I was glad I was staying there! Loved the covered entrance from parking. Helpful with rain. Feeling of ..."
Reviewed on Aug 22, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive, Pittsburgh, PA
Fully refundable
$119 nightly
The price is $136 total per night from Sep 1 to Sep 2
$136 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
"Beautiful hotel. Very modern."
Reviewed on Aug 25, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Aug 28 to Aug 29
$214 total
Aug 28 - Aug 29
Total with taxes and fees
9.2/10 Wonderful! (677 reviews)
"I travel quite a bit but this one really impressed me!"
Reviewed on Aug 16, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
4.5/5(843 reviews)
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
4.5/5(48 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
5/5(4 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Private City Kickstart Tour: Tokyo
$135
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
$47
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- University of Pittsburgh
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- Carnegie Museum of Art
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.